Negotiation Warriors
Negotiation Warriors, the podcast that features conversations with the greatest negotiators in professional sports.
Negotiation Warriors
Episode #010: Breaking Down the Salary Cap (Khai Harley)
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🎙️ Negotiation Warriors – Episode #010: Breaking Down the Salary Cap with Khai Harley
In Episode #010 of Negotiation Warriors, I sit down with one of the NFL’s top salary cap and contract strategists — Khai Harley, Senior Vice President of Football Operations and Assistant General Manager of the New Orleans Saints.
Over the course of his 23-year NFL career, Khai has become widely respected as one of the league’s leading experts in salary cap management, roster construction, contract negotiations, and the NFL Collective Bargaining Agreement. Working alongside Saints General Manager Mickey Loomis, Khai has helped build one of the NFL’s most stable and strategically disciplined front offices.
In this conversation, Khai opens up about:
• His unconventional journey from finance and Bloomberg to the NFL front office
• Working at the NFL Management Council and advising all 32 clubs on the salary cap and CBA
• Why emotional discipline and staying calm are critical traits for negotiators
• The importance of having a “walk away number” in every negotiation
• Why valuation must align with evaluation in player negotiations
• The reality of NFL roster construction and resource allocation under the salary cap
• Why some organizations consistently outperform others
• The role stability plays in front office success and decision-making
• How NFL teams identify overlooked talent and “diamonds in the rough”
• Why trusting your evaluation matters more than public perception
• The future impact of NIL and the transfer portal on talent evaluation
Khai also shares fascinating insight into how NFL front offices truly think about building winning rosters, balancing superstar contracts, managing long-term cap flexibility, and creating sustainable organizational success.
This episode is a masterclass in strategy, evaluation, emotional discipline, roster construction, and modern NFL negotiation philosophy.
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The scout has to see the player, right? Scout has to have conviction in the player. Then obviously, when you get the GM and everybody else on board, they're like, okay, let's give this guy a shot. Let's bring him in. But then sometimes it's also convincing the coaches, like, okay, give this guy a shot. Like, let's look at him, right? And then a lot of times the coaches might have some trepidation about the guy because he came from a small, small school, or because he's a small player and doesn't fit certain measurables. And then it's like, okay, well, trust what you see. So you have to have your coaches on board, you have to have the GM on board. And, you know, it's a it's a collective look at the player, a collective evaluation of the player to determine where he's and how he's going to help you win on Sunday.
SPEAKER_02Welcome to Negotiation Warriors. I am Cliff Stein, and I am on a never-ending quest to learn what it takes to be a great negotiator. In every episode, I will sit down with some of the greatest negotiators in professional sport who will share insight, knowledge, and role on their real life negotiations.
SPEAKER_03To find out how we are helping college athletic programs, go to Frontoffice360.com to schedule a demo. Welcome back to Negotiation Warriors, the podcast where we have conversations with some of the greatest negotiators in professional sports. Today's guest is my good friend Kai Harley, Senior Vice President of Football Operations and Assistant General Manager of the New Orleans Saints, a 23-year front office veteran. Kai has spent the last 18 seasons in New Orleans working alongside Mickey Loomis, leading contract negotiations, salary cap strategy, and roster management. He's widely respected as one of the league's top cap and CBA minds. He sits at the intersection of negotiation, strategy, and team building, which makes him a perfect guest for Negotiation Warriors. Welcome, Kai.
SPEAKER_00Hey, thanks a lot, Cliff. Always good to be with you and uh have a conversation. Looking forward to it.
SPEAKER_03Great to see you. First thing I want to say is you are the only person I know. I I don't meet a lot of people with my name, Cliff. And there's one person named Cliff Stein who I'm trying to get ahead of in the Google search because he's a math professor at Columbia. But I don't know any Kai's. I love that name, and there's no better name for a negotiation warrior than Kai Harley. What's the origin of the name Kai?
SPEAKER_00My mother read the name in Amistad, the book, and it was the name of a uh slave in the book, but then she changed the spelling and made it more of a Hawaiian spelling.
SPEAKER_01Now, why she did that, I have no idea. And I can say I run across several Kai's in my lifetime. We have a Kai on our roster right now, but he spells it K-A-I instead of K-H-A-I.
SPEAKER_03Okay, so I have an interesting fact for you. Do you know what Kai means in Scottish?
SPEAKER_01No, I don't.
SPEAKER_03Okay. Well, I was very pleased to find out that it means warrior, and which is perfect for the show, and it's a super powerful word to me because it applies in so many aspects of life. And one of the missions of negotiation warriors, obviously, we're finding what we consider master negotiations, but also to help people bring out their inner warrior in in every way to be become a better version and to be a better negotiator. So I love that your name means warrior, and I love that we informed you for the first time of that here on the show.
SPEAKER_01Yeah, that's cool. I mean, my mother always said that the African meaning of it was uh quiet strength. So I guess quite much like warrior similar. So I'll probably be able to do that.
SPEAKER_03Yeah, and I found that it's all positive. There are other meanings where it was good and strength and warrior. So I I love that. I love the the vibe that just even comes from the name because I do know you well and it does make sense that you have all these positive things. The other thing that I when I think of you, and I know this is probably an unintentional thing, is something you can't control, but the sound of your voice. Do you have you are you do you listen to or have you read um any of the Chris Voss, the the FBI negotiator? No. So he wrote the book Never Split the Difference, and one of his strategies as an FBI negotiator was the late night DJ voice. And the late night DJ voice was supposed to calm and soothe people. And actually, he sees science behind it that it creates neural changes in their brain because it gets them more comfortable and he was able to use it to talk to hostages. But I do think that you have a natural late-night DJ voice. Is that something that you've known that has helped you in negotiations or to keep negotiations calm just by the way your tone, your your personality?
SPEAKER_01Well, I I would say probably more my personality than my tone over the years. I would say sometimes, excuse me, sometimes it has even made negotiations with certain individuals more difficult from the standpoint of, I mean, you've probably experienced this where guys say things and they're trying to get a rise out of you. You know, they're trying to get you emotional about the situation. And when you stay calm, cool, and and collected, sometimes that throws them off, you know, or when when you counter a statement that they're trying to make with some facts and you do it in such a calm, matter-of-fact sort of tone, sometimes people don't know how to react to that, or and then they begin to be emotional about it. So I've experienced both in in my career, I would say.
SPEAKER_03Yeah, it's interesting. Like they really want to try to get uh a rise out of you or to read you, and you're you're hard to read because you have that that personality where you you're able to take emotion out of it. Let's go back a little bit though, like because you have a very interesting career path. And I I met you years ago. I've known you for well over 20 years. Tell me about how you get first began working in the NFL at any at any level.
SPEAKER_01Well, look, I I I started my career in finance. Um, I was a financial analyst for uh Bloomberg LP, working in um foreign the foreign bond market, basically. Um and I'm gonna say I got that job between the the summer of my between my sophomore and junior year of undergrad. Uh I got an internship. And then at the end of the summer, they offered me a full-time job, and then I stayed. So my last couple of years of undergrad, I was working full-time and going to school full-time. And I'm gonna say that first year after undergrad, I realized like I really didn't like the work. You know, I loved the people I worked with and I was good at my job, but I really didn't like the work and I wanted to pursue something different. And I always had an interest in the NFL and just never knew how exactly to go about doing it. And at that juncture, I figured my best opportunity was to go to grad school. And my background with numbers and finance, it seemed like a natural transition to try and work with contracts and the salary cap. So I went back to school and and got my master's degree, and then I turned that into an internship with the Colts, and then that turned to an internship with the Eagles, and then that turned into my first full-time position with the league in the player personnel department.
SPEAKER_03Yeah. So talk about when you were at the league. Like I I met you when you were with the management council, I believe. So you would have been um for me when I was uh a front office executive with the Chicago Bears, you know, there were often times that I needed someone at the league who could give me advice and guidance on the collective bargain agreement, on the salary cap, contract language. That was always you. Yeah. Tell us how the different roles you had when you're at the league and how it ended up at that role.
SPEAKER_01Well, primarily when I got into player personnel, part of that job was helping the other side on labor operations, labor relations manage and balance the cap each night. So it was part of the job, and then additional the player personnel rules and so forth. But after my first year in the league office in personnel, I moved directly over into labor relations. And from that point, your whole job is managing, you know, um, reviewing every contract that comes in for compliance with the cap and the constitution and bylaws, advising clubs on contract language, uh, evaluating every contract that comes in and making sure everybody's under the cap. Um, and then being in a support role for clubs in their uh negotiations. Um and you know, I did that for five and a half years before coming here to New Orleans.
SPEAKER_03And you obviously I know that I was calling you. Were were you getting that same is that your job? Like were all 32 teams calling you for guidance? Yeah. Awesome. Yeah, you were so good at it. And uh, and I was so happy when you got on the club side because I knew you you were you just knew so well. How did that though prepare you? Your experience at the management council, and how many, even before I ask you that, how many of you, how many contract negotiators do you even know are currently the came from the management council?
SPEAKER_01Um I haven't run a running total, but there's a number.
SPEAKER_03A number.
SPEAKER_01And and I would say what's what's happened is when clubs have openings, um, a lot of times the management council, labor relations, is the first place they look for somebody to come on because they know that person has had adequate training in the CBA and understands the CBA, and they figure like whether they're lead or whether they're in a support role, that they'll be an asset to negotiations going forward. So what you've seen over the years is some people have moved directly into the lead negotiating role, and then others have moved into a more secondary or even third role within clubs. But a lot of times they've gone to the management council for that. But I would also say that now in 2026, uh the the fifth uh viewpoint that people go to look for new people coming in is a lot wider than what it was 20-some years ago. You know, I would say 23, 24 years ago, it was almost exclusively either somebody from the management council or somebody who worked at an agency. And most teams had one person, maybe two. Now in 26, you're seeing a lot of teams have two, maybe three people in this area. So you've seen it grow over the years. But I would say like you know, I there there's at least ten that I can think of right off the top of my head. So um, you know, the number keeps keeps growing.
SPEAKER_03And you were again, you said you were accounting background, right?
SPEAKER_00Yes.
SPEAKER_03So for the students, whether they're business or law, and they want to do what you do, what would you say about them pursuing an opportunity to work at the management council as far as helping them get into a position like you are in right now?
SPEAKER_01Look, I would say there's many different roads to opportunity. Um and the the the league office has a number of different programs for students to come in and have internships, and they actually rotate different departments, and then there are separate departments that have have their own separate internships and they take people from a wide variety of backgrounds. Now, if you're going into labor ops on the legal side, obviously you need a legal background, but you can get access to negotiating salary cap exposure, if you will, and then same thing with player personnel or labor relations. So there are many different vehicles. I would say it's not as streamlined as maybe it was 20 years ago. The thing that I counsel young people on is really just to have an open mind as you move through it. I think certainly for myself, the way I've approached all of my jobs and dealing with the CAP, part of my accounting background, I think, has aided me and how I look at it. Now, will that be for everybody? I don't know. But I think when you look at the Constitution and bylaws, when you look at the CBA, I look at it similar to accounting professionals looking at gap principles. Is gap principles create a certain guideline, and yet there are only a few rigid black and white issues. There's a whole lot of gray. So it's like, okay, if it doesn't say I can't do it, then okay, I might do it. There might be some risk to it, but there's nothing preventing me from doing it. Right. So I think it's just a different way of looking at things and viewing things as you go through this.
SPEAKER_03Interesting. Yeah. Um, I always found that amazing. Like you you knew the CBA so well and you knew the language well, but you were not a lawyer. Then you didn't feel like that was not a disadvantage to you whatsoever in your NAT position and your current position.
SPEAKER_01No, I personally I think it was an asset. In my experience, what I would say is the league went through a period of time, call it 2006 through about 12, where they were almost exclusively looking for lawyers to fill a bunch of these positions. And yet I always focus more on the individual and the skill sets that the individual takes, you know, than the specific training. Because I think a lot of this job you can train somebody to do as long as they have the aptitude and and the willingness to learn and the willingness to know what they don't know and to be taught what they don't know. Um and I found that some of the lawyers who have entered the profession have looked at things in a little bit more black and white than maybe the gray areas that I just previously spoke of. So I just think it's been an asset for myself and how I've progressed in my career.
SPEAKER_03I love that. I love your perspective on that. And you're so right. The person is so important. Um, I'm gonna shift to I can't it's hard to talk to you about negotiations without talking about the salary cap and that obviously you're somebody who is a leading expert in that. So for for people that don't have the intricate knowledge that you you do, number one is what is it generally, and then also more importantly, what goes into what is cap management? What does that mean?
SPEAKER_01Look, whenever I get on and try to explain these things to students, I try and make it as simple, simple as possible, right? Um, and I will say that managing the cap, managing your roster is really just about resource allocation. Right? Is all 32 clubs get the same amount of resources? Now, again, there's there's some caveats there. Yeah, there are some serving some clubs that make more money than others, so they have a little bit more cash to spend. But because of the salary cap, the salary cap becomes the equalizer because over time you're all subject to the same rules, right? So you might spend over the cap, but yet, you know, it's going to catch up to you because you had to count it on every dollar you spend has to count on the cap at some point. So it really becomes how do you allocate a finite number of resources amongst your roster to produce the best team possible that actually results in a winning performance on the field.
SPEAKER_03Yeah. So you touched on a couple things. Number one, okay, so talk about team spending over the cap. First, the salary cap number that you work with comes to you from the basically the collective bargaining agreement, from the agreement between the union and the NFL.
SPEAKER_00Correct.
SPEAKER_03And in 2025, that number was right around 279 million, 279 million?
SPEAKER_00Yeah, 2792.
SPEAKER_03Okay. So if I'm an average fan, I'm obviously gonna think, well, that's how much money my team has to spend. But and you can correct me if I have the wrong numbers, but what my research shows that the team that spent the most in 2025 spent $348 million in cash, Jacksonville Jaguars. And the team that spent the least, and this is where I'm very proud of you, because I'm a cap guy, I'm not I'm not it was was the same. Is it 234 million? Now, again, I my numbers could be slightly off because this is what's reported. So that's a $90 million spread between the cap, or I'm sorry, and I mean, with the Jaguars spent $70 million above the cap. How do we explain that to people? Why is that so different?
SPEAKER_01That's when it goes back to what I said is it's about resource allocation and accounting, right? So when you amortizize something, you might spend all of it in one year, but yet you amortize it over a period of time. That's how, like, if again, you give a signing bonus, you have a five-year contract, and you give a guy $10 million in year one in terms of signing bonus, well, that only counts $2 million for each one of those years, even though you spent $10, only two count in that particular year, but then two counts in the four subsequent years after that. So in managing it, and why I say that the salary cap is that equalizer is you really can't consistently over an extended period of time spend that much over the salary cap, right? Because all that amortization comes back and counts at some point, right? So part of our load cash is also looking at some of our past spending catching up and us rebalancing, you know, our our our balance sheet, if you will, but you but you see that across the board, and that's the difference between our sport and basketball and baseball, right? So if you put all of our sports on a spectrum, you would say we're football's over here, basketball's in the middle, and baseball's over here. So basketball has a soft cap. But now they've tried to tighten it up in their last CBA somewhat, but it's still softer than ours. We have a hard cap. So in basketball, you can have a team like the Warriors who spend several hundred million over their cap. And, you know, we talk about the luxury apron apron and those sort of things. And you have these exceptions, Als, the high spending, high-revenue clubs to spend significantly more than the middle of the country. And it's the same thing in baseball with no cap, where you can have a team that spends more on two players than another team spends on their entire roster. In my humble opinion, I think that that's for us in the NFL, I think that's what's led to our growth and our prosperity and our popularity is the fact that you can have new teams and small markets competing with big markets on a regular basis because cash isn't what's going to be the overriding factor that determines whether or not your team is good or not.
SPEAKER_03All right. That's a great point because I'm going to ask you about that. But I wanted to first say thank you for saying Warriors, number one, the name of the podcast. It's also your name. So thank you for that. And then all and then, so from a money ball perspective, okay, do you you just said it. It's not the overriding reason for success. Do you study the correlation between spending and success or do any other kind of money ball analysis to help you make decisions?
SPEAKER_01Look, I've I've tried to do it, and it's what my my graduate school work was on was trying to correlate salaries and performance. And there were certain performance factors that correlate it negatively towards performance that people probably wouldn't think of, and some that correlated a little more positively. But again, over time, those things change because all of the factors that go into the valuation change, right? So we're in a world of everybody's touting analytics and what analytics can bring to the table, but what's the validity of your sample, right? And when you talk about all the variables that come into play, sometimes it's hard to make direct correlations. Um, and and one of the things I talk about sometimes is, you know, you go back to our Super Bowl team and probably do plus minus two years after that. And you would say, well, how much does offensive line spending go towards performance? Right? Well, we had two of the best four guards in football for four and a half, five years, and yet they were both on their rookie contracts. So was that a spend? Spending issue that gave us that edge where we weren't spending as much as other clubs? Or was it where we were at in the life cycle of the team? Is when you when you draft well and you complement that with good free agent signings, you know, you're you're going to have some level of success. But you do have to balance that out. So because we have a hard cap and because the top end of all of our rosters are increasing at a faster rate than the cap is increasing, you have to find people that are going to contribute at the lower end of the salary scale. You have to, right? Or else you are susceptible to injury, right? So if you have, you know, the majority of your roster and the majority of your talent all concentrated in a couple of high-value contracts and those players get hurt. And look, and look, we're in the business where people do get injured and you have to still feel the team. But when those players do get hurt, it does put a strain on the rest of your roster to be able to perform at the highest of levels. So oftentimes you find when you look at teams that do well to get to the postseason and into the postseason and in the postseason that oftentimes those are the healthiest teams in the league.
SPEAKER_03Right. And so if you ever in your studies, have you reached any conclusions on spending, or is it just more very situational based?
SPEAKER_01I would say it's on average it's more situational based. I can say I've I've probably found some things internally that I can't share with you that make a little bit more sense, but that's simply because we've been more stable than most clubs over the last 18 years. Right? So the fact that I can sit here 18 years in the league and say I'm been working for the same club, you know, as you well know, is is somewhat of an anomaly in our league. You don't find that too often. And then when you say that the GM has been here 20 years, and you could say we have a lot of staff that have been here 20 years, and we had a coach who was here for you know uh double digit years, it it provides a you know, when I talked about the validity of the sample, it provided more stability in those samples because the same decision makers were all at the table for most of that, right? So, you know, some of this you can think about, you know, situationally as like, is this more a when you look at what some other clubs do, is it more of a behavioral analysis than it is something quantitative based on the decision makers? So, you know, it's harder to gain a valid sample when you look at a club and they change decision makers three times in six years, right? So there there is something to say toward validity when you have the right people in place. And that, you know, as as you well know, when you change coaches, when you change GMs, you know, a lot of times those guys who replace them have a different viewpoint of how they're gonna structure the roster. So the first year or two of them being on the job, they might be trying to, you know, uh uh fit the team in their vision. And you know, you can't build Rome in a day, right? So it might take them till their third year to really get a clear vision and have a roster because most teams change over to roster 25 to 35 percent a year, right? So within three to four years, you're gonna have an entirely new roster for the most part, or 90% of your roster is gonna be changed over. But when you have, you know, stability, maybe that number dips down. And instead of having 90%, it's more 60%, you know, 65%. Um, and and you can look at what that's done to your overall performance and where your hits and misses are, and you can identify the reason behind some of those hits and misses because you have a little bit more information than looking at another club's operations from the outside.
SPEAKER_03All right. When we talk about hits and misses, building our roster, paying paying players, can't do any of it until we negotiate and sign them. You've been involved as a judge in mock negotiation competitions. There's a lot of newer people negotiating contracts now on the college level because of this new NIL world that was thrusted upon them. I think there's a perception that, and I'm teaching and you've done stuff, but there is a perception that uh, you know, maybe you just look at both a bunch of comps or statistics and come up with um a value. But I guess I want to ask you how important is the evaluation in getting to the evaluation to use it in negotiation?
SPEAKER_01I mean, it's incredibly important. Um, you know, I don't think that you can have, I don't think you can arrive at a quote unquote good contract intentionally without a genuine look and understanding of the evaluation of the player, right? So, you know, what we've tried to say here is like we're trying to marry the valuation to the evaluation and make sure that those things are in sync. And when when you do that, I think you get to the most important thing in any negotiation is understanding what your walkaway number is, right? So no matter what system you're in, whether you're in our system or whether you're in college dealing with NIL, um, you know, again, I I say I try and simplify these things for students. We negotiate things in our everyday life all the time. So whether you're negotiating a car, negotiating your mortgage, negotiating with your professor about whether or not you can get an extension for your time to get your project done, negotiating with your wife or how much time you could spend out with the boys, you're negotiating something. And yet when it comes to these things, like you got to have a walkaway number because if you don't, then the price is just gonna keep continue to go up. And as it goes up, if you do arrive at what's gonna be seen as quote unquote a good deal, you might have just gotten it by happenstance. You didn't necessarily get it on purpose. And I guess the best way to illustrate a uh, you know, the valuation in determining value is just because somebody's gonna be the highest paid at that position doesn't mean that that's value for you. So even with the evaluation of the player, where does the player fit within the nucleus of your roster? How does the player compliment or supplement the players on your roster? So, you know, you might say, hey, I want this guy to be, this guy is gonna make $15 million as a tight end, right? And he's gonna be most clubs' number one tight end. But for you in your club, you might have a good tight end who's already your number one tight end and like, well, this guy's only gonna be our number two. So even though the market price says this guy should be 15, is that value for you? Right. And I think that's where a lot of people miss out on it. Is like, look, I'm not saying I don't want this player. I'm not saying this player would be, you know, wouldn't be an asset to our team. The question is, are we going to get the most usage out of that player if we're gonna pay him as a number one, but only gonna play him as a number two or number three? Like, that just doesn't make a lot of sense. Like you're you're gonna end up, you know, not getting the bang for your buck that you expected for that deal or that you would want for that deal.
SPEAKER_03I I love that you said that you have a process where you're matching valuation to e-valuation. Everything you said struck with me is impactful. Uh but I want to I want to read something to you real quickly. So studying NFL teams, and I took a look at your roster, I found that 18 players or 23% of your roster, and now you I used 53 man, a practice squad, and some an injured reserve, and I found that 23% of your roster had were consisted of players that coming out of high school were either a zero-star rank player, whether they went to a uh Power 4 school or they were FCS players, you had six, group of five schools, seven, division two, you have one, even have one JUCO transfer. That's that's a significant portion of your roster. And so when we talk about evaluation from a 30,000-foot view, why are these players, and I know your your roster is not different than any other NFL team when we look at these numbers. Why are these players good enough for the NFL, but they're being missed by the top major college programs?
SPEAKER_01It's it's a somewhat complicated answer, I'll I'll tell you, because there's a lot of different factors. Because I will say it's not just the zero stars and where they're going to college, but it also occurs to certain college players coming from smaller schools and coming to our league, is sometimes it's about trusting what you see, right? So when the scouts go out on the road and they're they're looking, you know, are you trusting what you see or are you making excuses for what you see? Right? Because sometimes you you see a guy at a small school and you know, he seems to be running by everybody, but maybe doesn't have the production, you know, that that you would expect. And, you know, the the reality of it is is there there is some CYA that it that exists with some individuals, you know, in our in our world where the cover for the mistake is, well, this guy was graded high. Everybody had him graded high. You don't have to go out on as much of a limb for a guy who went to a Power Four school versus a guy who you know went to NAIA school. You don't have to jump out there and convince people that what you see is what you see. So there's certainly that aspect. And I think you can filter that down to the college at college world and say, hey, you know, if the guy just didn't get the views and get people looking at him for whatever reason, whether he went to a you know smaller group three school in his state versus a group one school in his state or group four school in his state, depending on, you know, obviously how that state evaluates their uh their high schools, might dictate how many eyeballs they got on them early. You know, like I I if I remember correctly, I think Josh Allen for a large part of his high school career played seven-on-seven football. Right? So, you know, sometimes it's just about seeing the talent and trusting what you see and being able to communicate that effectively to whoever the decision makers are to say, look, we're gonna get this guy, because at the end of the day, like that's where value will come from, right? Because when you find the quote unquote diamonds in the rough, you know, if I can take a step back when you we talk about the overall, you know, signing guys to contracts and so forth, well, there's also a supply and demand element to it, right? So again, as you're valuing and you're balancing the evaluation, well, sometimes that's affected by the market, right? So if the demand is high and you know the supply is low, then prices are gonna go up, right? So, you know, you you you you look at those things. And I think that occurs at the the high school and and collegiate level as well, where a guy who doesn't have stars, right? It's gonna be harder for somebody at the Indiana's, Miamis, Alabama's, and so forth, it's gonna be Ohio states to convince their staff that, hey, we need to go after this guy. We got value here. Wait a minute, we got a whole school full of four and five stars. Like, why are we gonna go for this zero star guy, right? And they have to go to the smaller school because that's where, you know, it's almost like somewhat of a popularity contest, unfortunately. But I think what we're seeing in in the collegiate world is I don't think that the situation is gonna be as stark as it's been in the past going forward because of NIL, right? So you're gonna have a wider distribution of talent amongst schools because of NIL and because of the transfer portal. And that's gonna transition into more of the PowerPoint, doing a lot more shopping in the portal for guys who have proven themselves at a smaller school than maybe what they would have done 10 years ago.
SPEAKER_03You said trusting your what you see, which I love because I think of a player right before you got there. One of the last players I represented as an agent was a guy named Michael Lewis. He was 29 years old, never played in college. I found him in the arena league, five foot seven, 165 pounds. He ran a 4'2 40. And the fact that one of your scouts, can't remember which one at the time, trusted what he saw, was willing to bring him in. And years later, now he becomes a Pro Bowl player for you. I think maybe even still works there or some kind of ambassador. That would have never happened if you didn't have an evaluator, whether it was your general manager or the scout, trusting what they saw and give him a chance.
SPEAKER_00Yeah. I mean, look, I I would say it takes a village, right?
SPEAKER_01Is it it's it's a whole organizational philosophy, if you will, is the scout has to see the player, right? Scout has to have conviction in the player. Then obviously, when you get the GM and everybody else on board, they're like, okay, let's give this guy a shot, let's bring him in. But then sometimes it's also convincing the coaches, like, okay, give this guy a shot. Like, let's look at him, right? And then a lot of times the coaches might have some trepidation about the guy because he came from a small, small school, or because he's a small player and doesn't fit certain measurables. And then it's like, okay, well, trust what you see, right? And a lot of times we get into the mode of people wanting players because they're familiar with the player, right? And say, well, they coached the player when when they were with this other club, they coached the player, they know what he's bringing to the table. Because that's what most people want is they don't like the volatility in play, right? So the guy that makes the great play but then gives up the great play, right? Like they want to know this is what I'm getting down in and down out, you know, without that volatility. And sometimes, you know, people will trust the people that they've been through it with it a little more than somebody who hasn't, right? So I'm like, man, well, we haven't seen this guy under the bright light, so what can he do? And it's collectively saying, you know what, everybody has a voice. Let's let's voice our um you know our evaluation of this player and let's give him his just due for what he's done. Let's not discount it because he went to a small school, let's not discount it because he wasn't drafted. Um, you know, if this guy is better than our fifth round draft choice, then he's earned the spot. And that doesn't happen everywhere, right? So you have to have your coaches on board, you have to have the GM on board, and you know, it's a it's a collective look at the player, a collective evaluation of the player to determine where he's and how he's gonna help you win on Sunday.
SPEAKER_03You know, people are everyone's fascinated by how much money professional athletes make. It's talked about every day in the in the in the media, and they assume they all make a lot of money. But when I study NFL rosters from highest to lowest paid on each team, once I get to about the 23rd, 24th player, highest paid player, pretty much starts to really go down. Like so maybe everyone else after that is probably 1.5 and lower, close to the minimum, actually. And that's not a little amount of money, obviously, but but compared to what the top end players make, why do you think that is? Why do you think that the majority of your roster actually probably makes closer to the minimum than they do to what the highest paid players make?
SPEAKER_01Well, uh it it goes back to resource allocation and the fact that whatever system you have, superstars are gonna get more than their fair share. That they just are, right? Um, so I will say there's probably a little more stratification than what you mentioned. Um, like I think if you went back 20 years ago, you would say, you know, 12 to 15 players made up about 75% of your cap. Right. And I think if you looked at that across the board today, it's probably more closer to six players making that. Right. But you still have to still have to field 53 and you still have to have 16 guys on the practice squad, right? So you're still trying to make all of this fit within the confines of a hard cap, right? So you have more players um, you know, taking up that amount, um, and the it's more weighted towards the top end of your roster, um, and then you have your guaranteed increases of minimum salaries every year. So, you know, when when you look at it, the overall increase uh in the cap from you know 2002 to 2025, you're gonna come up with a certain percentage, right? But if you look at almost every position in the league, uh when you look at the highest paid players, have far outseed, out you know, outpaced that percentage increase. So you, you know, it and I and I would say it's probably not that much different than the rest of the country, and like the middle class is getting squeezed. Um, and it's just that's the way you balance it out. It's like, well, we have to have these players on one end because they're helping us win, and they're the most talented, and they've come up for free agency and they've earned the contract that they're getting. But you know, the flip side to that is like the more I pay them, the less I have to pay everybody else. So it becomes critical to determine if the players in question are genuinely worth that amount of money. Again, the valuation and looking at what the market is going to pay them versus their impact on your team and figuring out whether that's the wisest decision to make. Um, so I I I would say balancing that out and marrying the evaluation to the valuation is probably more critical in today's game in 2026 than it's ever been.
SPEAKER_03And then, like you said, you have that many players, whether they're backups or role players, you can get away with paying that amount because, like you said, supply and demand is going to be factored into how much you have to pay them. Yeah. I want to be conscious of your time because Mickey Loomis is in the other room and he's staring at um a board and he's like, I need Kai to help with this. And please tell Mickey I said hello. But I do want to ask you one one last question that we do ask all of our guests, and and I think you would have great uh insight knowing how you think. But what are the key characteristics of a great negotiator?
SPEAKER_01First and foremost, I think you got to be true to yourself in in who you are. Don't try to be, you know, who uh you think a good negotiator is gonna be. Right? Don't try to be who you know you read in a book if that's not your personality. Right. Um, you know, you you you mentioned my calm voice. Like, I'm calm when I come into these things. So if I tried to be the fire and brimstone guy, there's not gonna be any authenticity in that. That's not my personality. So first and foremost, I would say, hey, be who you are and learn different aspects to negotiation and incorporate that into your own personality in your own way of how you're going to approach things. Two, I would say you you have to be knowledge and be aware of both the pros and the cons of a negotiation. What do you expect the other side to come come back to you with? Know the answers before you ask the question and know what questions they're gonna have before they ask them. So be prepared and be knowledgeful. Um and then three, I would say again, as I said earlier, have a walkaway number and don't be afraid to walk away. Sometimes the best deals of the deals you don't get done. History has shown that. Like we all have deals that we regret doing, and we all got deals that we're happy we didn't get done, right? So as long as you're true to those three things, then I think you'll be you'll fare fairly well.
SPEAKER_03Amazing. I knew you wouldn't disappoint, and I'm so grateful for your time. I Harley, he's a negotiation warrior. He his name means warrior. So he's an excellent guest, and uh, that's a big takeaway for him. But uh great, great job, Kai. Really appreciate having you and uh good luck in all the stuff you got to do in the offseason. I got your work cut out for you.
SPEAKER_01So again, appreciate all of your time. Hey, I appreciate having you having me on the show and uh look forward to our next conversation. Great. All right, we'll talk to you soon. Thanks, Kai.
SPEAKER_02Thank you, thank you for listening to Negotiation Warriors. Hope you enjoyed this episode. If you like what you heard, please subscribe on the Negotiation Warriors YouTube channel and follow us at FunOffice360 on Instagram and at find out our helping college athletic programs for funoffice360.com.